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Bangkok, Thailand
Start with streetfood in Yaowarat (Chinatown) on your first evening. Day two covers Wat Pho, the Grand Palace and Wat Arun at sunset — bring a long trousers or sarong. Day three goes quirky: Talad Noi streetart, Lumpini Park monitor lizards and Khao San Road at night.
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Ayutthaya, Thailand
Rent a bicycle and explore the ancient ruins: don't miss the Buddha head entwined in tree roots at Wat Mahathat and the riverside Wat Chaiwatthanaram at sunset. Try roti saimai — sweet cotton-candy roti — from the market stalls near the old city. Catch the overnight sleeper train to Chiang Mai; book first class well in advance via the official D-Ticket site or 12Go.
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Chiang Mai, Thailand
Base yourself at Stamps Backpackers in the Old City and explore Wat Chedi Luang, Wat Phra Singh and the tunnel temple Wat Umong. Highlights include a Thai cooking class with market visit, a full day at the ethical Elephant Nature Park (book weeks ahead), and the Sunday Walking Street. Squeeze in two dental appointments — general checkup and crown placement — and rent a scooter for the Mae Hong Son loop.
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Pai, Thailand
The legendary 762-bend road from Chiang Mai leads to this laid-back mountain valley beloved by backpackers. Spend a day visiting the Land Split, Pai Canyon at sunset, Boon Ko Ku So bamboo bridge and the Santichon Yunnan village. Don't miss the lively Pai Walking Street in the evenings.
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Mae Hong Son, Thailand
En route, stop at Tham Lod river cave for a bamboo-raft ride through the cavern and the dramatic swallow exodus at dusk. The twin Burmese-style temples Wat Jong Kham and Wat Jong Klang reflect beautifully on the central lake in the morning mist. Day-trip to the Yunnan tea village Ban Rak Thai on the Myanmar border, plus the Su Tong Pae bamboo bridge and serene Pang Ung lake.
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Mae Sariang, Thailand
A quiet, largely tourist-free river town marking the southern stretch of the Mae Hong Son loop — 160 km of beautiful, empty mountain road from Mae Hong Son. It makes a perfect overnight stop before the final push back to Chiang Mai via Doi Inthanon. The local market and riverside temples are worth a slow evening stroll.
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Khao Sok, Thailand
One of Thailand's most spectacular national parks, centred on Cheow Lan Lake surrounded by dramatic limestone karsts. Take an overnight lake tour sleeping in floating raft huts, swim in the jade-green water and trek the Nam Talu cave with a headlamp. Early mornings reward with gibbons calling across the lake and hornbills in the canopy.
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Koh Tao, Thailand
Thailand's top budget diving island, with excellent snorkelling at Shark Bay even without a certification. Rent a scooter to loop the hilly island roads and catch a snorkel tour to the outer reefs. Check the Escobar Jungle Party calendar (kohtaoescobar.com) for their UK Garage and Drum & Bass night — wear closed shoes in the jungle venue.
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Koh Phangan, Thailand
Stay near Ban Tai or Thong Sala rather than the chaotic Haad Rin for a more relaxed base. The Jungle Experience party — a drum-and-bass and fire-show event in the jungle near Ban Tai — falls the night before the Full Moon Party (around 22 December for the full moon on 23 December). Buy tickets online in advance around 1000 THB and keep an eye on phangan.events and the Jungle Experience social channels for confirmed dates.
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Koh Lanta, Thailand
Long Beach (Phra Ae) is a mellow base for Christmas week — beach bars do festive seafood dinners and the island pace is perfect for recovery. Ride a scooter south to Kantiang Bay, the Mu Ko Lanta National Park viewpoint and the charming wooden shophouses of Lanta Old Town. Don't miss the Time for Lime cooking class (proceeds support Lanta Animal Welfare) and an optional day trip by speedboat to Railay's limestone cliffs and Phra Nang cave beach.
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Phuket, Thailand
Arrive in time for New Year's Eve: Patong Beach hosts a massive countdown with fireworks and Bangla Road delivers full-on nightlife if you want it, while Phuket Old Town offers a more atmospheric celebration. Spend New Year's Day recovering in the Sino-Portuguese Old Town with Hokkien mee at Mee Ton Poe and dim sum at Lock Tien food court. Consider a Phang Nga Bay tour for James Bond Island and sea-cave kayaking before flying to Phnom Penh.
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Phnom Penh, Cambodia
Start with the Royal Palace and Silver Pagoda, then stroll Sisowath Quay along the Mekong for a sunset river cruise. Dedicate a full day to Tuol Sleng S-21 prison and the Killing Fields of Choeung Ek — leave the rest of that day unscheduled, as both sites are emotionally heavy. The Russian Market is the best spot for cheap souvenirs and local lunch.
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Battambang, Cambodia
Cambodia's most charming provincial city, with elegant French colonial architecture lining the Sangkae River. Ride the legendary bamboo train — a wooden platform on railway axles rattling across old tracks — and catch the bat exodus from the caves of Phnom Sampeau at dusk, with its sobering killing cave memorial. An evening show at the Phare Ponleu Selpak circus school is one of Southeast Asia's most memorable cultural experiences.
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Siem Reap, Cambodia
Buy your Angkor temple pass on arrival — a three-day pass (around 62 USD) covers two solid temple days with room to spare. Rise before dawn for Angkor Wat at sunrise, then spend the morning at Angkor Thom and the face-covered Bayon; on the second temple day explore Ta Prohm with its tree roots consuming the stone walls and the intricate carvings of Banteay Srei. End the trip with a morning boat tour to the authentic floating villages of Kampong Phluk or Kompong Khleang on the Tonle Sap lake and a hands-on Khmer cooking class making fish amok.